Get financial advice on whether the move makes economic sense. Factor in not only a new salary, but also a different cost of living, moving expenses and varying real-estate markets. Moving is a sizable financial investment, with the average relocation within Canada costing about $50,000. Transporting household goods are the single biggest part of any moving expense.
Enticing a mid-career family to move to Pittsburgh doesn't make much sense. Choose your boomerang migrants carefully. Bring back entrepreneurial talent if you insist on spending your budget on this demographic. A better idea along these lines would be some sort of diaspora mentorship such as Globalscot given that many shrinking cities don't have enough of entrepreneurial executive experience.
I would do a regional audit of worker shortages and then figure out the top talent production locations in this field. College graduates can relocate on the cheap. Young adults (and immigrants) are innovative when it comes to dealing with a high cost of living. Short of direct financial remuneration to incentivize the move your region, you might fund a Bulldogs in the Bluegrass program.
I've read about a number of programs that seek to match local businesses with local graduates. The genius of Bulldogs is that it introduces new people to the charms of Louisville (among other cities). Rust Belt cities in particular need to break into new networks and establish different path dependent migrations. I could see Bruins in the Burgh or Cardinal at Carnegie placing talented interns at promising startups (e.g. PeaceMaker or Etcetera Edutainment). I could see AlphaLab or even the Pittsburgh Technology Council running this type of initiative. The hope is to establish fresh talent pipelines and increase network in-migration.